Pyridine → HCID 75231415, compound

HRID 602817Notes

Reaction equation

HRID 602817 reaction equation
[C:1]1([S:7]([C:10]([CH:19]2[CH2:31][C:22]3[NH:23][C:24]4[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][C:29]=4[C:21]=3[CH2:20]2)([F:18])[C:11]2[O:15][N:14]=[C:13]([CH2:16][NH2:17])[N:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:32][C:33]([F:38])([F:37])[C:34](O)=[O:35].N1C=CC=CC=1>C(Cl)Cl>[C:1]1([S:7]([C:10]([CH:19]2[CH2:31][C:22]3[NH:23][C:24]4[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][C:29]=4[C:21]=3[CH2:20]2)([F:18])[C:11]2[O:15][N:14]=[C:13]([CH2:16][NH:17][C:34](=[O:35])[C:33]([F:38])([F:37])[F:32])[N:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 11453978HCID 11453978, compound

Product 1

HCID 75231415HCID 75231415, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 46 mg (0.1 mmol) of (RS,SR)-C-{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-yl}-methylamine in 3 mL CH2Cl2 at RT, was added 10 μl (0.1 mmol, 1 eq) trifluoroacetic acid and 80 μl pyridine (1 mmol, 10 eq). Stirring was continued overnight, and the reaction mixture was evaporated to dryness. Column chromatography on silica gel (heptane/EtOAc 6:4) yielded 6 mg (12%) of (RS,SR)-N-{5-[benzenesulfonyl-(7-chloro-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-fluoro-methyl]-[1,2,4]oxadiazol-3-ylmethyl}-2,2,2-trifluoro-acetamide as a light yellow powder, MS: 557 (MH+).

Workup

  1. customthe reaction mixture was evaporated to dryness

Sources & evidence

ORD record
ord-24c949dfcc19490b8df1d5cba4159d8c
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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